Even in totalitarian regimes, freedom of thought presumably cannot be outlawed, provided that such thought remains unspoken and unwritten. In Australia, freedom of expression is taken-for-granted. This paper sets out to theorise my teaching practice/s, as I enact some of my theories. It emerges from my recent attempts to encourage in my students a greater sense of empathy towards others, and adoption of a multiplicity of perspectives. The contexts in which the study is embedded include immigration (to Australia) and attitudes to Indigenous Australians, but the teaching approaches described here can be applied to other similar contexts internationally. The paper outlines and evaluates related teaching strategies. Questions posed by the paper include: what are the internal mechanisms that limit our thought with regard to social issues such as equality? What are the teaching/learning approaches that we might employ to help our students transcend these limitations? Can freedom of thought only function in the context of self-regulation? In other words, where, if anywhere, are the "natural limits" of freedom of thought, and are there times when freedom of thought is not desirable or acceptable? If so, who decides and how? What are the implications for the power differential between teacher and student? (Contains 1 figure.)